Darien Vacations from $248

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Darien Vacation

There's tons to love about Darien, from its rich history to its spectacular views. When you're ready to spend some time in this captivating city, our Darien vacation packages will be perfect for you. If your trip to Darien includes some sightseeing, hit up well-known attractions like Morton Arboretum, Promenade Bolingbrook and Cog Hill Golf & Country Club. Whatever your travel plans or budget, organizing a tailored Darien vacation is easy with Expedia.

The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $366, price is now $248 per person
$248
per person
Jan 14 - Jan 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,491, price is now $479 per person
$479
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $518, price is now $300 per person
$300
per person
Jan 14 - Jan 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Breakfast buffet was amazing. Would definitely stay here again.

Reviewed on Oct 30, 2026

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,110, price is now $685 per person
$685
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $692, price is now $463 per person
$463
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Darien
View all trips

Stay near popular Darien attractions

National Shrine of St. Therese

7.4/10 (6 reviews)
This tranquil shrine houses the largest collection of St. Therese's personal effects outside France. Explore the museum's first-class relics and replica convent cell before reflecting in the serene garden sanctuary.
See properties

What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

$24
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
See all activities in Darien

Darien Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $124 total per night from Nov 10 to Nov 11
$124 total
Nov 10 - Nov 11
Total with taxes and fees
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $131 total per night from Nov 26 to Nov 27
$131 total
Nov 26 - Nov 27
Total with taxes and fees
River Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $158 total per night from Nov 27 to Nov 28
$158 total
Nov 27 - Nov 28
Total with taxes and fees
8.6/10 Excellent! (3,497 reviews)
"Very kind and excellent staff. The property was beautiful and lively"

Reviewed on Oct 30, 2026

Hilton Chicago
See all 3,928 properties in Darien
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Darien Vacation Packages

Darien Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
22,300
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Galloping Ghost and DuPage Childrens Museum

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from $248 on Expedia. However, how much your vacation to Darien costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Darien?
If you're looking to book a cheap Darien vacation package, consider visiting in January, June and August. You'll typically find better prices on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Darien?
With a well-organized schedule, you can easily hit the top Darien attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Darien vacation for longer.
How to find the best Darien package deals?
Use Expedia's handy filters to help you find some of the best Darien package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Darien package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Darien vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Darien?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Darien vacation.
Does Expedia offer Book Now, Pay Later Darien vacation packages?
Set off on your dream trip to Darien with our Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up bargains while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.